With world-class dining and nightlife, spas and shopping, and activities from snorkeling to Segways, Bermuda is the ideal destination for a group of friends ready to explore all that the island has to offer. Lauren Maggard of Jet Set World Travel has created an itinerary that covers the entire island, from west to east. More importantly, her trip plan includes activities that will appeal to every member of your entourage.

Lauren's itinerary includes opportunities to visit some of Bermuda's most popular nightlife options and try the island's signature drinks, like the Dark 'n' Stormy. The Harbourfront Restaurant and Tobacco Bay are two of her top choices but she can share other favorite spots on her long list of top restaurants, bars, and pubs.

Trip Designer

Lauren Maggard

Lauren Maggard, a luxury travel consultant at Jet Set World Travel, received a masters in contemporary art and worked at an auction house before pursuing a career in travel. A member of AFAR's Travel Advisory Council, Lauren creates active itineraries to destinatiions around the world.

Day 1

Wander the West End

After landing in Bermuda, get settled at Elbow Beach Resort. Conveniently located with the capital, Hamilton, less than 10 minutes away, you’ll enjoy the privacy that comes with the 50 acres of landscaped grounds here. Next head to the West End to zoom around on a Segway tour, with stops at Frog & Onion in the Royal Naval Dockyard for pub grub—skip dessert and head to the Bermuda Rum Cake Company. After a post-lunch stroll, don flippers to explore Snorkel Park. End the afternoon with some culture at the Bermuda National Museum before heading back to Elbow Beach, sated from a day of activity, for dinner at the resort’s Café Lido overlooking the beach with stunning ocean views.

Day 2

Meet Me in the Middle

Ease into your second day at the Elbow Beach spa with treatments like the Ocean Body Wrap and release those toxins you stored up and then breathe in ocean breezes. Next, head to Hamilton for some shopping. Many popular stores can be found on Front Street, facing the harbor, from boutiques selling island-inspired fashions to jewelers with original designs. Check out TABS at A.S. Coopers, Urban Cottage, and the perfumes at Lili Bermuda, as well as landmarks like the Session House and the stately white City Hall. Start the evening with cocktails at the Harbourfront Restaurant, followed by dinner at Bolero—we can arrange to reserve the balcony for your group.

Day 3

End on the East End

On your final day, travel back to the island's earliest days as you explore the East End. St. George's is Bermuda's oldest town, where George Sommers first set foot in 1609. The old stocks provide an Instagram moment, but your day won't be punishing—instead head to Meltdown on Old Cellar Lane fro a scoop of ice cream in one of the signature flavors. At David Rose Jewelry, pick up a unique piece to remember your trip. (On Saturdays, Meet the Designer events let you learn about the jewelry design from two masters.) Start your evening at Tobacco Bay, where there's always a beach party, and then head to 1609 at the Hamilton Princess & Beach Club to say goodbye to Bermuda over a dinner harborside.